a-chymotrypsin-catalyzed transesterification in toluene using polystyrene resins containing hydrophilic groups and amino groups as a support.

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Crosslinked polystyrene resins containing N-butylamino, N, N-dimethylamino, and N, N-diethylamino groups with or without spacer chains were used as supports to make α-chymotrypsin (CT) function efficiently in organic solvents. The enzymatic activity of the immobilized CT was measured for transesterification of N-Ac-L-PheOEt with propyl alcohol in toluene. At low levels of loading of the amino groups, the activity of CT was poor. Introduction of hydrophilic groups such as quaternary ammonium salts or tetraethyleneglycol to the amine-attaching resins, however, greatly enhanced the CT activity, while the hydrophilic groups alone did not exhibit significant improvements. With an increase in amine loading to the resin, the final yield of AcPheOPr rather decreased together with the increasing yield of hydrolysis product, AcPheOH. This tendency seems to be strengthened as the basicity of the amino groups becomes larger. The resin in which the N-butylamino groups were neutralized by AcPheOH afforded an excellent rate of formation of AcPheOPr without further accumulation of AcPheOH. The roles of amino groups and hydrophilic groups were discussed on the basis of these results.
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